反应详情

Bicine (0.95 g, 5.82×10−3 mol, Aldrich®, 99+%) was added to chloroform (30 mL, anhydrous, Aldrich®, 99+%). A concentrate of docosanoyl chloride, prepared by the reaction of docosanoic acid (4.12 g, 1.14×10−2 mol, Aldrich®) with excess oxalyl chloride (Sigma) in chloroform, was added dropwise to the suspension. After stirring for a few minutes, excess pyridine (1.5 mL, anhydrous, Aldrich®, 99+%) was added to the flask. The flask was refluxed overnight. The reaction mixture was acidified with dilute HCl saturated with sodium chloride (Mallinckrodt, AR®). The aqueous phase was separated. Any remaining volatiles were removed from the organic phase under reduced pressure with mild heating. The glassy product was recrystallized from ethanol (Mallinckrodt, AR®). The product was recovered by filtration as an amorphous white solid. The product weighed 2.86 g after vacuum drying for a 61% yield; mp 73-75° C.; Rf=0.23 (silica gel, 10:1; chloroform-methanol). 1H NMR (CDCl3, 99.8% D, 1% TMS, Aldrich): 0.880 ppm (t,); 1.254 ppm (s); IR (paraffin oil) OH 3,100 cm−1; CO 1,760 and 1,700 cm−1 C—O 1,180 cm−1.

1. concentrationA concentrate of docosanoyl chloride
2. additionwas added dropwise to the suspension
3. temperatureThe flask was refluxed overnight
4. customThe aqueous phase was separated
5. customAny remaining volatiles were removed from the organic phase under reduced pressure with mild heating
6. customThe glassy product was recrystallized from ethanol (Mallinckrodt, AR®)
7. filtrationThe product was recovered by filtration as an amorphous white solid
8. customdrying for a 61% yield